We all make mistakes.

I’ve made a few mistakes in my time. I’m not talking about the garden-variety mistakes you might make in the course of the day. I’m talking about product development whoppers, or the kind you look back on several years later and wonder, “What was I thinking!?”

You make the best decision you can based on the information you know at the time and your framework for making decisions. There are a few decisions I wish I could take back, because if I could change them now, they would be great companies (or at least, I could feel like I made the right decision 10 years later). They were ideas for products that I still want now, that still solve a concrete problem, and that people are still willing to pay money to solve. (These ideas also work because they enable the businesses that use them to make more money and get more yield out of their current investment.)

What was my biggest mistake?

My Biggest Mistake was not trusting myself to make the right decision with the information I knew at the time. I didn’t have all of the answers – how to execute, how to find the money, how to deal with the ups and downs of being an entrepreneur – and I let that feeling of being out of my comfort zone make my decision for me. The lesson for next time? Be comfortable with being uncomfortable. Trust my gut more, and be in the moment when struck by a big idea that wants to be real.

Now, you decide whether I should have gone forward.

Here are the ideas that I had and decided not to do. Read them with the knowledge that you have in 2013, and decide whether you would pursue them today: I would.

Big Idea: Make the Grocery Store Easier.

Idea #1: Imagine if the next time you went into your local grocery store, there was a way for your phone to tell you the location of every product in the store, to remember your past preferences for shopping, and even to direct you in an optimal aisle-by-aisle route to minimize the time in store? And what if you received loyalty rewards and marketing offers that pertained to you? And what if you could check out of the store simply by scanning each item with your phone as you placed into the cart. That idea sounds promising and real in 2013, and quite similar to the idea my friends are pursuing at qThru.

When I thought of a very similar idea in 1999, even though the hardware and software was off the shelf and readily available, I didn’t go and build it. I made the decision that “I wasn’t the type to do that,” and “I’m not an idea guy” and let self-doubt make my decision for me. I can’t have that decision back, and I know that what I was really feeling in the moment was, “oh crap. I have no idea how to even begin thinking about that much less how to build and monetize it.” And, it happened again.

Big Idea #2: Make Waiting at a Restaurant Better.

Idea #2: Imagine you arrive at a popular restaurant. Because they are very busy, they ask you for your phone number so that they can text message you when your table is available. At the same time, they ask you to join their loyalty program so that you can participate in drink specials, learn about special events, and play games or trivia while you are waiting in line. It exists today – it’s called TurnStar – and I’ve used it. It’s pretty slick.

Why didn’t I build my version? It was called TextMyTable, and I was ready to go with the vision, the business plan, and the execution play. It was September 2008. Then all of a sudden the economy did a flip-flop and all of our assumptions about what was a normal business turned on their head. Or did they? I was stuck because I didn’t know how to raise the money to start the business or to grow the business in such a way that it generated operating capital.

What’s the Commonality?

In both of these ideas (and in others it’s not important to share here), I had an idea for a product or a service that was innovative. The ideas capitalized on a consumer need, solved an actual problem and had a reasonable chance at being successful. We could argue about the size of the market and the relative degree of success, and the fact remains that they were good ideas. And I made a mistake in not pursuing them.

What did I learn and what would I do next time?

The first thing I learned is that you can’t find out whether you’ll succeed with an idea until you try it. (Duh.) The ideas I think that would have been successful might have been abject failures, wild successes, or more likely somewhere in between. And I don’t know because I didn’t try them.

The second thing I learned from these mistakes is that collaboration is everything. I needed to do more to ask people to tear apart the idea instead of trying to build the whole business from start to finish inside my head. Groups like Startup Edition are a great place to get feedback, learn from other perspectives, and to reframe your questions.

And finally, I learned from my mistakes that it’s impossible to know what you don’t know until you do it. (Sounds like a Zen koan, doesn’t it.) What can you do about that? Admit that you’re going to make mistakes. Try to make different ones the next time you approach a problem, and learn from the results. Trust your gut.